Dimethylamine → {3-[3-(Dimethylamino)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}-(morpholin-4-yl)methanone

HRID 661269Notes

Reaction equation

HRID 661269 reaction equation
Cl[C:2]1[N:6]=[C:5]([CH:7]2[CH2:12][CH:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[CH2:10][N:9]([C:23]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:24])[CH2:8]2)[O:4][N:3]=1.[CH3:31][NH:32][CH3:33]>C(O)C>[CH3:31][N:32]([CH3:33])[C:2]1[N:6]=[C:5]([CH:7]2[CH2:12][CH:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[CH2:10][N:9]([C:23]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:24])[CH2:8]2)[O:4][N:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 58116540{3-(3-Chloro-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}(morpholin-4-yl)methanone

Product 1

HCID 49819288{3-[3-(Dimethylamino)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}-(morpholin-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 158 mg (0.355 mmol) of the oxadiazole from Example 23A in 2.5 ml of ethanol were added 2.50 ml (19.7 mmol, 40% in water) of dimethylamine solution, and then the reaction mixture was stirred in the microwave at 80 for 1 h. The solvent was removed under reduced pressure and the crude product was purified by means of preparative HPLC. Yield: 94.0 mg (58% of theory)

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-5f54af752ae24ace94fe39a4b7234ea3
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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